I get asked this question fairly often, and I now have a lot
of data on what works, so I thought I’d share my response.

Usually, people are deciding between going to college (and
usually working on side projects while they do so), joining a company, or
starting their own startup. [1] [2]

The secret is that any of these can be right answer, and you
should make your decision based on the specific circumstances of each
option. The critical point is that you
want to do the thing that is most likely to get you on a path to do something
great.

No matter what you choose, build stuff and be around smart
people. “Stuff” can be a lot of
different things—open source projects outside of class, a startup, a new sales
process at a company you work at—but, obviously, sitting around talking with
your friends about how you guys really should build a website together does not
count.

The best people always seem to be building stuff and hanging
around smart people, so if you have to decide between several options, this may
be a good filter.

Working on something good will pull you along a path where
good things keep happening to you. (In
fact, this effect is so strong that there’s a danger of getting sucked into too
many interesting things and getting distracted from what you really want to
do.)

In making this decision, you want to take the right kind of
risk. Most people think about risk the
wrong way—for example, staying in college seems like a non-risky path. However, getting nothing done for four of
your most productive years is actually pretty risky. Starting a company that you’re in love with
is the right kind of risk. Becoming
employee number 50 at a company that still has a good chance of failure is the
wrong kind of risk.

If you stay in college, make sure you learn something
worthwhile and work on interesting projects—college is probably the best place
to meet people to work with. If you’re
really worried you’ll miss some critical social experience by dropping out of
college, you should probably stay.

If you join a company, my general advice is to join a
company on a breakout trajectory. There
are a usually a handful of these at a time, and they are usually identifiable
to a smart young person. They are a very
good risk/reward tradeoff. Such a
company is almost certainly going to be successful, but the rest of the world
isn’t quite as convinced of it as they should be. Fortunately, these companies love ambitious
young people. In addition to the equity
being a great deal (you might get 1/10th of the equity you’d get if
you join a tiny new startup, but at 1/100th or 1/1000th
of the risk), you will work with very good people, learn what success looks
like, and get a W on your record (which turns out to be quite valuable). Spending a few years at a company that fails
has path consequences, and working at an already-massively-successful company
means you will learn much less, and probably work with less impressive people.

Incidentally, don’t let salary be a factor. I just watched someone turn down one
of these breakout companies because Microsoft offered him $30k per year more in
salary—that was a terrible decision. He
will not build interesting things and may not work with smart people. In a few years, when it’s time for something
new, the options in front of him will be much worse than they could have been.

If you start a company, only do so if you have an idea
you’re in love with. If you’re hanging
out with your friends trying to come up with an idea, I don’t think you should
start that company (although there are many who disagree with me). Starting a failed startup is less bad than
joining a failed company as an employee (and you’ll certainly learn much more
in the former case). If you fail at an
idea that you really loved and could have been great, you’re unlikely to regret
it, and people will not hold it against you. Failing at a me-too copycat
startup is worse. Remember that there
will be lots of other opportunities to start companies, and that startups are a
6-10 year commitment—wait for the right one

One big pro for starting a company is that it’s usually the
way to learn the most in the shortest amount of time. One big con is that it’s easy to start a
company for the wrong reasons—usually so that you can say you’re starting a
company—and this makes it easy to cloud your judgment.

No matter what you choose, keep your personal burn rate low
and minimize your commitments. I have
seen a lot of people miss great opportunities because they couldn’t afford a
reduction in salary or because they couldn’t move or didn’t have the time.

Think about risk the right way. Drew Houston gave a great commencement speech
where he said you only have to be right once.
That’s true. The risk is not
getting on the path where you get to be right that one critical time.

Thanks to Lachy Groom and Nick Sivo for reading drafts of
this.

[1] Sometimes, a 4th option is being a VC. This is usually a mistake—the best way to become
a VC is not to grind your way up the ladder from junior associate intern. Even if you want to be a VC, you’re much
better off starting or joining a startup, and getting partner offers when
you’re 28. Plus, good founders want to
work with an investor that has operational experience.

Enter your email address to get email alerts about new posts on this site.
Unsubscribe anytime.

Email address is invalid.

394 responses

Garry Tan
upvoted this post.

Joseph Walla
upvoted this post.

A posthaven user
upvoted this post.

Jordan Lee
upvoted this post.

In regards to [2], I as well think that is interesting. I have a solid idea that I am in love with, but plan go to college to meet other people who can give me feedback on the idea (15,000 potential beta users/people to validate the idea? Yes please!) and then help build it (depending on the size of the project most others won't need the help). Plus, having an immediate market to launch your product into is great. Imagine trying to launch Facebook without Harvard? If Zuckerberg built Facebook out in the Valley it would've ended up as "another social network". By building and launching (in this case exclusively) at Harvard, He had his peers to quickly use, validate, and share the idea which spread like wildfire (and kept spreading due to the way the site was distributed).
College offers a chance to connect with like-minded people and start something great. In this sense, I think that most people overlook college because they see it as a distraction when in reality, it's ripe full of opportunities. *Plus having a college degree will be immensely helpful for future job opportunities (if the startup fails) because most (non-startups) won't hire you if you don't have a degree.

—
Cameron

I bet the guy who turned down the offer really wanted to go with the breakthrough young company.

—
Fvom Leibmer

Lots of good stuff here-hard to break away from the social norms of going to college, etc but if you see a fat pitch you should take it as you point out.

—
Adrian Meli

Rune Sørensen
upvoted this post.

Yeah, it's such a bad idea to take a job at MICROSOFT instead of gambling with startups. You're a shitheel.

—
Pillory

Advice only for 19 year olds? Much of this advice applys to anyone wanting to do interesting things.

—
Chris Bruno

"my general advice is to join a company on a breakout trajectory"
I couldn't understand the meaning of' breakout trajectory'.
please explain.

—
anant

How can we know which companies are on a breakout trajectory?

—
h

^ There isn't a way to tell for sure, but you can use your good judgement and knowledge of the startup world to determine if:
1) The idea is solid and there is a demand for the product. (Don't join a startup that you don't have 100% confidence in)
2) It has gained some traction, or has the potential to gain traction.
If you keep those two things in mind, you will have a higher probability of joining a company on the success track.

—
Cam

I have only one complaint about this post .. the title. This advice seems as applicable to an ambitious 29 year old, or for that matter an ambitious 59 year old, as to an ambitious 19 year old...
"The critical point is that you want to do the thing that is most likely to get you on a path to do something great."
Why wouldn't that apply to my dad (or mom)!?

—
Arjun Vasan

why are people so concerned with the title? do they think your going to go change the title or something? haha, like c'mon now.. haha.
anyways, dang man, thanks thats some great advice dude.
helpful article, your doing a good thing! :P

—
Sammyboy

convincing

—
Michael Taku Vezha

Interestingly, I have considered, and definitely want to do [2]. Then again, I'm not a CS major. Still, lots of good advice, however, do you really believe startups are 6-10 years of commitment? With the way acquisitions seem to be happening, wouldn't 3-7 be a more appropriate number?